Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_section_title ; Isomorphic supramolecular structures via one-dimensional hydrogen bonding motifs in crystals of chiral difluorolactates, trichlorolactates and trifluorolactates ; _publ_contact_author_name 'Dr Toshimasa Katagiri' _publ_contact_author_address ; Applied Chemistry Okayama University Tsushimanaka 3-1-1 Okayama 700-8530 JAPAN ; _publ_contact_author_email tkata@cc.okayama-u.ac.jp _publ_section_references ; teXsan Single Crystal Structure Analysis Software. Version 1.11 - Molecular Structure Corporation, Rigaku Corporation. (2000). . MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. WinGX - Farrugia, L. J. (1999) J. Appl. Cryst. 32, 837. PLATON/PLUTON - Spek, A. L. (1990) Acta Cryst. A46, C34. MERCURY - Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.; Macrae, C. F.; McCabe, P.; Pearson J.; Taylor, R. (2002) Acta Cryst. B58, 389. ; loop_ _publ_author_name 'Satoshi Takahashi' 'Tatsuya Jukurogi' 'Toshimasa Katagiri' 'Kenji Uneyama' data_(R)-4 _database_code_depnum_ccdc_archive 'CCDC 292296' _audit_creation_method SHELXL-97 _audit_update_record ; 2005-12-8 CheckCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Isopropyl-(R)-(-)-3,3-difluorolactate _chemical_melting_point 335 _chemical_formula_moiety 'C6 H10 F2 O3' _chemical_formula_sum 'C6 H10 F2 O3' _chemical_formula_weight 168.14 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -2.21 (c= 1.38, MeOH)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.2602(4) _cell_length_b 9.2900(10) _cell_length_c 16.674(3) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 814.81(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 6269 _cell_measurement_theta_min 8.1 _cell_measurement_theta_max 54.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_special_details ;This compound tends to sublimate at room temperature. A needle crystal was mounted on a glass capillary quickly and quick-freezed by cold nitrogen flux of a low temperature device. The crystal was cooled during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ; '(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS IV imaging plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6180 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 27.43 _reflns_number_total 1043 _reflns_number_gt 996 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.4 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atom of OH have been located from Fourier difference map and fixed to its position. The remaining H-atoms were included in caluculated position. and treated as riding atoms using the SHELXL default parameters. Large displacement parameters for two methyl C atoms of the isopropyl group were indicative of positional disorder. The disorderd isopropyl group were refined using PART instruction of SHELXL (C5&C6: part1, C7&C8: part2) with occupancy factors of 0.6(for part1):0.4(for part2). Refinement of this disorderd model gave significantly improved R values. [R1 = 0.066, wR2 = 0.18 (before) >> R1 = 0.0346, wR2 = 0.0888 (after)] Even with this disorder model, some displacement parameters remain high and the geometry in the isopropyl group is somewhat unreliable. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0514P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (R)-2,2-difluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Freidel pairs were merged before refinement. ; _refine_ls_number_reflns 1043 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.218 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.6312(3) 1.11755(13) 0.52751(8) 0.0568(4) Uani 1 1 d . . . F2 F 0.2498(3) 1.04067(17) 0.55404(7) 0.0634(4) Uani 1 1 d . . . O1 O 0.5687(2) 0.81975(12) 0.50575(6) 0.0281(3) Uani 1 1 d . . . O2 O 0.8730(2) 0.88811(13) 0.38376(7) 0.0311(3) Uani 1 1 d . . . O3 O 0.5840(2) 1.04245(13) 0.33351(7) 0.0312(3) Uani 1 1 d . A . C1 C 0.4156(4) 1.0640(2) 0.49330(11) 0.0392(4) Uani 1 1 d . . . H2 H 0.3436 1.1347 0.4542 0.047 Uiso 1 1 calc R . . C2 C 0.4738(3) 0.92256(16) 0.45183(8) 0.0236(3) Uani 1 1 d . . . H3 H 0.3145 0.8847 0.4268 0.028 Uiso 1 1 calc R . . C3 C 0.6705(3) 0.94781(15) 0.38652(8) 0.0215(3) Uani 1 1 d . . . C4 C 0.7512(4) 1.0815(2) 0.26597(11) 0.0387(4) Uani 1 1 d . . . C5 C 0.9342(9) 1.1886(5) 0.2901(2) 0.0538(10) Uani 0.60 1 d P A 1 H5A H 1.0335 1.2191 0.2434 0.081 Uiso 0.60 1 calc PR A 1 H5B H 1.0483 1.1477 0.3306 0.081 Uiso 0.60 1 calc PR A 1 H5C H 0.8452 1.2718 0.3128 0.081 Uiso 0.60 1 calc PR A 1 C6 C 0.5693(10) 1.1273(5) 0.1985(2) 0.0556(10) Uani 0.60 1 d P A 1 H6A H 0.6656 1.1410 0.1488 0.083 Uiso 0.60 1 calc PR A 1 H6B H 0.4857 1.2178 0.2133 0.083 Uiso 0.60 1 calc PR A 1 H6C H 0.4406 1.0524 0.1905 0.083 Uiso 0.60 1 calc PR A 1 C7 C 0.650(2) 1.0414(10) 0.1941(4) 0.080(3) Uani 0.40 1 d P A 2 H7A H 0.7627 1.0731 0.1506 0.120 Uiso 0.40 1 calc PR A 2 H7B H 0.4827 1.0858 0.1875 0.120 Uiso 0.40 1 calc PR A 2 H7C H 0.6333 0.9364 0.1924 0.120 Uiso 0.40 1 calc PR A 2 C8 C 0.769(2) 1.2533(9) 0.2741(4) 0.094(4) Uani 0.40 1 d P A 2 H8A H 0.8605 1.2926 0.2279 0.142 Uiso 0.40 1 calc PR A 2 H8B H 0.8603 1.2780 0.3235 0.142 Uiso 0.40 1 calc PR A 2 H8C H 0.5974 1.2940 0.2760 0.142 Uiso 0.40 1 calc PR A 2 H4 H 0.859(7) 0.989(4) 0.254(2) 0.082(10) Uiso 1 1 d . B 1 H1 H 0.4522 0.7603 0.5246 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0769(10) 0.0387(6) 0.0549(7) -0.0146(5) 0.0070(7) -0.0162(7) F2 0.0716(10) 0.0696(9) 0.0490(7) -0.0038(6) 0.0361(7) 0.0078(8) O1 0.0245(5) 0.0287(5) 0.0311(5) 0.0138(4) -0.0003(4) -0.0034(4) O2 0.0262(6) 0.0374(6) 0.0297(5) 0.0100(4) 0.0034(4) 0.0080(5) O3 0.0299(6) 0.0352(6) 0.0287(5) 0.0138(4) 0.0041(4) 0.0077(5) C1 0.0473(10) 0.0362(8) 0.0342(8) 0.0015(7) 0.0144(8) 0.0071(7) C2 0.0210(7) 0.0254(7) 0.0244(6) 0.0057(5) -0.0007(5) 0.0006(5) C3 0.0226(7) 0.0203(6) 0.0216(6) 0.0023(5) -0.0016(5) -0.0005(5) C4 0.0431(10) 0.0432(10) 0.0299(8) 0.0170(7) 0.0103(7) 0.0091(8) C5 0.055(2) 0.060(2) 0.0472(19) 0.0206(18) 0.0061(17) -0.0163(19) C6 0.072(3) 0.067(3) 0.0271(15) 0.0200(17) -0.0063(17) 0.002(2) C7 0.117(8) 0.079(5) 0.044(3) -0.020(3) 0.035(4) -0.034(5) C8 0.168(10) 0.069(5) 0.047(4) -0.010(3) 0.038(5) -0.067(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.363(3) . ? F2 C1 1.354(2) . ? O1 C2 1.4036(17) . ? O1 H1 0.880 . ? O2 C3 1.2021(18) . ? O3 C3 1.3271(17) . ? O3 C4 1.474(2) . ? C1 C2 1.516(2) . ? C1 H2 1.0000 . ? C2 C3 1.5202(19) . ? C2 H3 1.0000 . ? C4 C5 1.441(5) . ? C4 C6 1.536(4) . ? C4 C7 1.363(8) . ? C4 C8 1.604(8) . ? C4 H4 1.05(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 114.00 . . ? C3 O3 C4 117.86(13) . . ? F2 C1 F1 106.34(15) . . ? F2 C1 C2 109.40(15) . . ? F1 C1 C2 109.82(15) . . ? F2 C1 H2 110.4 . . ? F1 C1 H2 110.4 . . ? C2 C1 H2 110.4 . . ? O1 C2 C1 111.68(13) . . ? O1 C2 C3 108.76(12) . . ? C1 C2 C3 109.29(12) . . ? O1 C2 H3 109.0 . . ? C1 C2 H3 109.0 . . ? C3 C2 H3 109.0 . . ? O2 C3 O3 125.73(13) . . ? O2 C3 C2 124.02(12) . . ? O3 C3 C2 110.24(12) . . ? C7 C4 C5 134.0(4) . . ? C7 C4 O3 111.9(4) . . ? C5 C4 O3 110.8(2) . . ? C5 C4 C6 115.4(3) . . ? O3 C4 C6 104.8(2) . . ? C7 C4 C8 111.7(5) . . ? O3 C4 C8 102.4(3) . . ? C6 C4 C8 79.8(5) . . ? C7 C4 H4 79.5(18) . . ? C5 C4 H4 105.0(19) . . ? O3 C4 H4 105.5(18) . . ? C6 C4 H4 115.0(18) . . ? C8 C4 H4 143.1(19) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? H7A C7 H4 98.2 . . ? H7B C7 H4 146.7 . . ? H7C C7 H4 76.8 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F2 C1 C2 O1 -56.7(2) . . . . ? F1 C1 C2 O1 59.70(18) . . . . ? F2 C1 C2 C3 -177.05(14) . . . . ? F1 C1 C2 C3 -60.69(17) . . . . ? C4 O3 C3 O2 -1.5(2) . . . . ? C4 O3 C3 C2 179.38(14) . . . . ? O1 C2 C3 O2 -0.4(2) . . . . ? C1 C2 C3 O2 121.73(17) . . . . ? O1 C2 C3 O3 178.68(12) . . . . ? C1 C2 C3 O3 -59.16(16) . . . . ? C3 O3 C4 C7 116.3(5) . . . . ? C3 O3 C4 C5 -81.4(3) . . . . ? C3 O3 C4 C6 153.5(2) . . . . ? C3 O3 C4 C8 -123.9(5) . . . . ? #END #------------------------------------------------------------------------------ data_(R,R)-5a _database_code_depnum_ccdc_archive 'CCDC 292297' _audit_creation_method SHELXL-97 _audit_update_record ; 2005-12-8 CheckCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Hexamethylene-(R,R)-bis(3,3-difluorolactate) _chemical_melting_point 356 _chemical_formula_moiety 'C12 H18 F4 O6' _chemical_formula_sum 'C12 H18 F4 O6' _chemical_formula_weight 334.26 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -5.72 (c= 0.81, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 18.8223(6) _cell_length_b 5.14670(10) _cell_length_c 7.7739(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 753.08(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 7965 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 54.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_special_details ; A platelet crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.694 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; '(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS IV imaging plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 5840 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1043 _reflns_number_gt 945 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.4 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.0446P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (R)-difluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Freidel pairs were merged before refinement. ; _refine_ls_number_reflns 1043 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.216 _refine_ls_restrained_S_all 1.216 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.264 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.060 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.57004(9) 0.8242(4) 0.5692(3) 0.0399(5) Uani 1 1 d . . . F2 F 0.58875(9) 1.2054(4) 0.4575(2) 0.0429(5) Uani 1 1 d . . . O1 O 0.71446(10) 0.9496(3) 0.5068(2) 0.0241(4) Uani 1 1 d . . . O2 O 0.72274(9) 0.6709(3) 0.7972(2) 0.0239(4) Uani 1 1 d . . . O3 O 0.64581(9) 0.9389(3) 0.9325(2) 0.0171(4) Uani 1 1 d . . . C1 C 0.59675(14) 1.0635(6) 0.6034(4) 0.0257(6) Uani 1 1 d . . . C2 C 0.67523(12) 1.0437(5) 0.6482(3) 0.0172(5) Uani 1 1 d . . . H3 H 0.6930 1.2160 0.6801 0.021 Uiso 1 1 calc R . . C3 C 0.68480(12) 0.8601(5) 0.7985(3) 0.0161(5) Uani 1 1 d . . . C4 C 0.65133(14) 0.7868(5) 1.0920(3) 0.0209(5) Uani 1 1 d . . . H4A H 0.6392 0.8964 1.1891 0.025 Uiso 1 1 calc R . . H4B H 0.7000 0.7289 1.1068 0.025 Uiso 1 1 calc R . . C5 C 0.60271(13) 0.5538(5) 1.0892(4) 0.0217(5) Uani 1 1 d . . . H5A H 0.6120 0.4493 1.1905 0.026 Uiso 1 1 calc R . . H5B H 0.6141 0.4490 0.9892 0.026 Uiso 1 1 calc R . . C6 C 0.52361(13) 0.6202(4) 1.0845(4) 0.0200(5) Uani 1 1 d . . . H6A H 0.5120 0.7264 1.1837 0.024 Uiso 1 1 calc R . . H6B H 0.5138 0.7218 0.9821 0.024 Uiso 1 1 calc R . . H2 H 0.5662(15) 1.149(6) 0.696(4) 0.020 Uiso 1 1 d . . . H1 H 0.7321 1.0704 0.4496 0.039 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0263(8) 0.0501(10) 0.0435(10) -0.0042(11) -0.0069(8) -0.0118(9) F2 0.0395(10) 0.0654(13) 0.0238(9) 0.0194(10) 0.0021(8) 0.0157(11) O1 0.0266(9) 0.0213(8) 0.0244(9) 0.0029(8) 0.0131(8) 0.0005(9) O2 0.0226(8) 0.0218(8) 0.0272(10) 0.0014(8) 0.0015(9) 0.0088(9) O3 0.0205(8) 0.0159(7) 0.0150(8) 0.0001(8) 0.0022(7) 0.0003(7) C1 0.0247(13) 0.0324(14) 0.0199(13) 0.0065(12) -0.0010(12) 0.0048(14) C2 0.0172(11) 0.0159(11) 0.0185(12) 0.0002(10) 0.0058(10) 0.0015(11) C3 0.0112(9) 0.0187(10) 0.0185(11) -0.0020(11) -0.0009(10) -0.0017(10) C4 0.0261(12) 0.0230(11) 0.0136(11) 0.0001(11) -0.0026(11) -0.0011(11) C5 0.0300(12) 0.0174(10) 0.0178(12) 0.0067(11) 0.0010(12) -0.0010(12) C6 0.0252(11) 0.0145(10) 0.0203(11) -0.0014(10) 0.0012(10) -0.0029(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.357(3) . ? F2 C1 1.357(3) . ? O1 C2 1.410(3) . ? O1 H1 0.830 . ? O2 C3 1.207(3) . ? O3 C3 1.337(3) . ? O3 C4 1.470(3) . ? C1 C2 1.521(3) . ? C1 H2 1.02(3) . ? C2 C3 1.513(4) . ? C2 H3 0.9800 . ? C4 C5 1.508(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.528(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C6 1.523(4) 2_665 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 112.0 . . ? C3 O3 C4 117.17(18) . . ? F1 C1 F2 106.5(2) . . ? F1 C1 C2 110.1(2) . . ? F2 C1 C2 109.6(2) . . ? F1 C1 H2 108.7(16) . . ? F2 C1 H2 107.0(16) . . ? C2 C1 H2 114.6(16) . . ? O1 C2 C3 108.98(19) . . ? O1 C2 C1 110.7(2) . . ? C3 C2 C1 109.5(2) . . ? O1 C2 H3 109.2 . . ? C3 C2 H3 109.2 . . ? C1 C2 H3 109.2 . . ? O2 C3 O3 125.1(2) . . ? O2 C3 C2 124.6(2) . . ? O3 C3 C2 110.29(19) . . ? O3 C4 C5 111.6(2) . . ? O3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? O3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 114.4(2) . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C6 C6 C5 112.8(2) 2_665 . ? C6 C6 H6A 109.0 2_665 . ? C5 C6 H6A 109.0 . . ? C6 C6 H6B 109.0 2_665 . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 O1 63.5(3) . . . . ? F2 C1 C2 O1 -53.3(3) . . . . ? F1 C1 C2 C3 -56.7(3) . . . . ? F2 C1 C2 C3 -173.5(2) . . . . ? C4 O3 C3 O2 1.8(3) . . . . ? C4 O3 C3 C2 -177.64(18) . . . . ? O1 C2 C3 O2 3.0(3) . . . . ? C1 C2 C3 O2 124.3(2) . . . . ? O1 C2 C3 O3 -177.47(18) . . . . ? C1 C2 C3 O3 -56.3(3) . . . . ? C3 O3 C4 C5 -83.9(2) . . . . ? O3 C4 C5 C6 -64.8(3) . . . . ? C4 C5 C6 C6 -179.16(16) . . . 2_665 ? #END #------------------------------------------------------------------------------ data_(S)-6 _database_code_depnum_ccdc_archive 'CCDC 292298' _audit_creation_method SHELXL-97 _audit_update_record ; 2005-12-8 CheckCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Isopropyl-(S)-(-)-3,3,3-trichlorolactate _chemical_melting_point 316 _chemical_formula_moiety 'C6 H9 Cl3 O3' _chemical_formula_sum 'C6 H9 Cl3 O3' _chemical_formula_weight 235.48 _chemical_absolute_configuration ad _chemical_optical_rotation '[\a]^20^~D~= -23.0 (c=0.506, MeOH)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.6464(3) _cell_length_b 5.64350(10) _cell_length_c 10.8654(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.4510(10) _cell_angle_gamma 90.00 _cell_volume 499.93(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5435 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_special_details ;This compound sublimates slowly at room temperature. A platelet crystal was mounted on a glass capillary and quick-freezed by cold nitrogen flux of a low temperature device. The crystal was cooled during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8072 _exptl_absorpt_correction_T_max 0.9005 _exptl_absorpt_process_details ; NUMABS Higashi T. (1999) Program for absorption correction, Rigaku Corporation, Tokyo, Japan. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS 4 imaging plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 3871 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2150 _reflns_number_gt 2128 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.4 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(6) _refine_ls_number_reflns 2150 _refine_ls_number_parameters 111 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.347 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.068 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.72216(5) 0.66903(8) 0.75527(4) 0.01732(11) Uani 1 1 d . . . Cl2 Cl 0.64727(6) 0.22371(8) 0.85211(4) 0.01846(12) Uani 1 1 d . . . Cl3 Cl 0.47165(6) 0.64717(8) 0.87446(4) 0.01837(12) Uani 1 1 d . . . O1 O 0.51439(19) 0.3572(3) 0.55260(14) 0.0185(3) Uani 1 1 d . . . O2 O 0.31020(19) 0.0532(3) 0.59188(15) 0.0210(3) Uani 1 1 d . . . O3 O 0.21959(17) 0.3081(3) 0.71064(15) 0.0182(3) Uani 1 1 d . . . C1 C 0.5619(2) 0.4914(4) 0.77407(18) 0.0120(3) Uani 1 1 d . . . C2 C 0.4347(2) 0.4393(4) 0.63657(19) 0.0130(3) Uani 1 1 d . . . H2 H 0.3726 0.5872 0.6001 0.016 Uiso 1 1 calc R . . C3 C 0.3144(2) 0.2435(4) 0.64327(18) 0.0142(4) Uani 1 1 d . . . C4 C 0.1070(2) 0.1286(4) 0.7310(2) 0.0209(4) Uani 1 1 d . . . H4 H 0.1575 -0.0321 0.7363 0.025 Uiso 1 1 calc R . . C5 C 0.0877(3) 0.1898(7) 0.8606(2) 0.0352(6) Uani 1 1 d . . . H5A H 0.1957 0.1913 0.9288 0.053 Uiso 1 1 calc R . . H5B H 0.0179 0.0712 0.8821 0.053 Uiso 1 1 calc R . . H5C H 0.0370 0.3466 0.8549 0.053 Uiso 1 1 calc R . . C6 C -0.0520(2) 0.1367(5) 0.6172(2) 0.0262(5) Uani 1 1 d . . . H6A H -0.0992 0.2961 0.6101 0.039 Uiso 1 1 calc R . . H6B H -0.1292 0.0215 0.6313 0.039 Uiso 1 1 calc R . . H6C H -0.0305 0.0979 0.5365 0.039 Uiso 1 1 calc R . . H1 H 0.5427 0.4680 0.5007 0.028 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0183(2) 0.0147(2) 0.0198(2) -0.00072(16) 0.00745(16) -0.00578(16) Cl2 0.0205(2) 0.0130(2) 0.0205(2) 0.00543(17) 0.00507(17) 0.00255(17) Cl3 0.0214(2) 0.0190(3) 0.0171(2) -0.00698(17) 0.00955(17) -0.00072(17) O1 0.0257(7) 0.0200(8) 0.0148(7) -0.0044(5) 0.0135(6) -0.0060(6) O2 0.0215(7) 0.0191(8) 0.0262(8) -0.0080(6) 0.0129(6) -0.0070(6) O3 0.0149(6) 0.0222(8) 0.0197(7) -0.0030(6) 0.0085(6) -0.0018(6) C1 0.0145(8) 0.0115(9) 0.0115(8) -0.0011(7) 0.0062(7) -0.0009(7) C2 0.0135(8) 0.0144(9) 0.0110(8) 0.0001(6) 0.0039(7) -0.0016(7) C3 0.0130(8) 0.0160(10) 0.0125(8) 0.0001(7) 0.0029(6) -0.0006(7) C4 0.0131(8) 0.0276(13) 0.0230(10) 0.0056(9) 0.0073(7) -0.0001(8) C5 0.0176(9) 0.069(2) 0.0196(10) 0.0089(13) 0.0070(8) -0.0009(12) C6 0.0160(9) 0.0369(15) 0.0233(10) 0.0011(9) 0.0034(8) -0.0074(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7762(19) . ? Cl2 C1 1.769(2) . ? Cl3 C1 1.7716(19) . ? O1 C2 1.393(2) . ? O1 H1 0.9300 . ? O2 C3 1.205(3) . ? O3 C3 1.319(2) . ? O3 C4 1.472(2) . ? C1 C2 1.560(3) . ? C2 C3 1.536(3) . ? C2 H2 1.0000 . ? C4 C5 1.512(3) . ? C4 C6 1.513(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 118.0 . . ? C3 O3 C4 117.20(17) . . ? C2 C1 Cl2 110.29(14) . . ? C2 C1 Cl3 111.61(13) . . ? Cl2 C1 Cl3 109.12(10) . . ? C2 C1 Cl1 108.94(13) . . ? Cl2 C1 Cl1 108.67(10) . . ? Cl3 C1 Cl1 108.14(10) . . ? O1 C2 C3 106.39(17) . . ? O1 C2 C1 110.18(15) . . ? C3 C2 C1 111.28(15) . . ? O1 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C1 C2 H2 109.6 . . ? O2 C3 O3 125.12(19) . . ? O2 C3 C2 122.36(17) . . ? O3 C3 C2 112.52(18) . . ? O3 C4 C5 105.45(19) . . ? O3 C4 C6 108.83(17) . . ? C5 C4 C6 113.70(18) . . ? O3 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? C6 C4 H4 109.6 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C1 C2 O1 -69.50(19) . . . . ? Cl3 C1 C2 O1 169.02(15) . . . . ? Cl1 C1 C2 O1 49.7(2) . . . . ? Cl2 C1 C2 C3 48.25(19) . . . . ? Cl3 C1 C2 C3 -73.22(19) . . . . ? Cl1 C1 C2 C3 167.44(14) . . . . ? C4 O3 C3 O2 3.8(3) . . . . ? C4 O3 C3 C2 -175.98(15) . . . . ? O1 C2 C3 O2 6.0(3) . . . . ? C1 C2 C3 O2 -114.0(2) . . . . ? O1 C2 C3 O3 -174.14(16) . . . . ? C1 C2 C3 O3 65.8(2) . . . . ? C3 O3 C4 C5 149.66(18) . . . . ? C3 O3 C4 C6 -88.0(2) . . . . ? #END #------------------------------------------------------------------------------ data_(S,S)-7b _database_code_depnum_ccdc_archive 'CCDC 292299' _audit_creation_method SHELXL-97 _audit_update_record ; 2005-12-8 CheckCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common (-)-Octamethylene-(S,S)-bis(3,3,3-trichlorolactate) _chemical_melting_point 357 _chemical_formula_moiety 'C14 H20 Cl6 O6' _chemical_formula_sum 'C14 H20 Cl6 O6' _chemical_formula_weight 497.03 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^20^~D~= -12.7 (c = 0.63, MeOH)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 21.7785(17) _cell_length_b 5.7582(2) _cell_length_c 8.4827(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1063.77(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 12994 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 150(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_special_details ;A platelet crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details ; '(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(1) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 8008 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1352 _reflns_number_gt 1222 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.4 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.0780P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ;Flack H D (1983), Acta Cryst. A39, 876-881 The Flack parameter was too large to determine the absolute configuration. So Friedel pairs were merged before final refinement cycle. ; _refine_ls_abs_structure_Flack 0.41(14) _refine_ls_number_reflns 1352 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.311 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.88407(5) 1.15482(18) -0.10871(12) 0.0409(3) Uani 1 1 d . . . Cl2 Cl 0.90450(5) 0.71611(19) 0.04642(15) 0.0498(3) Uani 1 1 d . . . Cl3 Cl 0.92418(4) 1.14679(19) 0.21224(12) 0.0384(3) Uani 1 1 d . . . O1 O 0.77243(11) 0.9195(5) 0.0033(3) 0.0355(7) Uani 1 1 d . . . O2 O 0.77271(11) 0.6572(5) 0.2542(3) 0.0368(6) Uani 1 1 d . . . O3 O 0.82046(10) 0.9292(5) 0.3983(3) 0.0273(6) Uani 1 1 d . . . C1 C 0.87746(17) 1.0020(6) 0.0725(4) 0.0293(8) Uani 1 1 d . . . C2 C 0.80931(15) 1.0021(7) 0.1252(4) 0.0260(7) Uani 1 1 d . . . H2 H 0.7969 1.1606 0.1526 0.031 Uiso 1 1 calc R . . C3 C 0.79896(14) 0.8430(6) 0.2659(4) 0.0257(7) Uani 1 1 d . . . C4 C 0.81123(17) 0.7928(8) 0.5426(4) 0.0316(8) Uani 1 1 d . . . H3A H 0.7696 0.7330 0.5439 0.038 Uiso 1 1 calc R . . H3B H 0.8162 0.8934 0.6334 0.038 Uiso 1 1 calc R . . C5 C 0.85552(16) 0.5934(8) 0.5554(5) 0.0349(9) Uani 1 1 d . . . H4A H 0.8493 0.4900 0.4666 0.042 Uiso 1 1 calc R . . H4B H 0.8465 0.5068 0.6507 0.042 Uiso 1 1 calc R . . C6 C 0.92258(17) 0.6687(7) 0.5590(5) 0.0353(9) Uani 1 1 d . . . H5A H 0.9313 0.7587 0.4650 0.042 Uiso 1 1 calc R . . H5B H 0.9290 0.7690 0.6494 0.042 Uiso 1 1 calc R . . C7 C 0.96725(18) 0.4687(8) 0.5679(6) 0.0415(10) Uani 1 1 d . . . H6A H 0.9587 0.3812 0.6631 0.050 Uiso 1 1 calc R . . H6B H 0.9596 0.3666 0.4790 0.050 Uiso 1 1 calc R . . H1 H 0.7547 1.0365 -0.0458 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0590(6) 0.0349(5) 0.0287(4) 0.0046(4) 0.0026(4) -0.0098(5) Cl2 0.0540(6) 0.0247(5) 0.0706(8) 0.0012(5) 0.0185(6) 0.0110(4) Cl3 0.0308(4) 0.0442(6) 0.0403(5) 0.0048(5) -0.0078(4) -0.0093(4) O1 0.0440(15) 0.0304(16) 0.0319(14) 0.0073(12) -0.0204(13) -0.0050(12) O2 0.0434(14) 0.0372(16) 0.0297(14) 0.0022(13) -0.0063(12) -0.0149(13) O3 0.0267(12) 0.0319(15) 0.0235(12) -0.0031(11) -0.0026(10) 0.0043(10) C1 0.0337(18) 0.0219(18) 0.0322(19) -0.0011(15) 0.0025(16) -0.0012(15) C2 0.0256(16) 0.0266(18) 0.0258(16) 0.0007(16) -0.0088(14) -0.0010(14) C3 0.0240(16) 0.0274(18) 0.0258(17) -0.0034(16) -0.0042(14) 0.0032(15) C4 0.0287(17) 0.041(2) 0.0249(17) -0.0001(17) 0.0030(15) 0.0027(16) C5 0.0364(19) 0.039(2) 0.0292(17) 0.0067(18) -0.0027(17) 0.0028(17) C6 0.0338(17) 0.038(2) 0.0345(19) -0.0008(19) 0.0001(17) 0.0026(17) C7 0.0350(18) 0.042(2) 0.048(2) 0.005(2) -0.0071(19) -0.0001(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.777(4) . ? Cl2 C1 1.762(4) . ? Cl3 C1 1.771(4) . ? O1 C2 1.393(4) . ? O1 H1 0.880 . ? O2 C3 1.217(4) . ? O3 C3 1.314(4) . ? O3 C4 1.468(5) . ? C1 C2 1.550(5) . ? C2 C3 1.521(5) . ? C2 H2 0.9800 . ? C4 C5 1.504(5) . ? C4 H3A 0.9700 . ? C4 H3B 0.9700 . ? C5 C6 1.524(6) . ? C5 H4A 0.9700 . ? C5 H4B 0.9700 . ? C6 C7 1.509(5) . ? C6 H5A 0.9700 . ? C6 H5B 0.9700 . ? C7 C7 1.471(8) 2_765 ? C7 H6A 0.9700 . ? C7 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 110.0 . . ? C3 O3 C4 117.5(3) . . ? C2 C1 Cl2 110.9(3) . . ? C2 C1 Cl3 110.9(2) . . ? Cl2 C1 Cl3 109.4(2) . . ? C2 C1 Cl1 109.1(2) . . ? Cl2 C1 Cl1 109.1(2) . . ? Cl3 C1 Cl1 107.4(2) . . ? O1 C2 C3 107.0(3) . . ? O1 C2 C1 109.7(3) . . ? C3 C2 C1 111.6(3) . . ? O1 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? O2 C3 O3 124.7(3) . . ? O2 C3 C2 122.3(3) . . ? O3 C3 C2 113.0(3) . . ? O3 C4 C5 112.4(3) . . ? O3 C4 H3A 109.1 . . ? C5 C4 H3A 109.1 . . ? O3 C4 H3B 109.1 . . ? C5 C4 H3B 109.1 . . ? H3A C4 H3B 107.9 . . ? C4 C5 C6 113.5(4) . . ? C4 C5 H4A 108.9 . . ? C6 C5 H4A 108.9 . . ? C4 C5 H4B 108.9 . . ? C6 C5 H4B 108.9 . . ? H4A C5 H4B 107.7 . . ? C7 C6 C5 113.7(4) . . ? C7 C6 H5A 108.8 . . ? C5 C6 H5A 108.8 . . ? C7 C6 H5B 108.8 . . ? C5 C6 H5B 108.8 . . ? H5A C6 H5B 107.7 . . ? C7 C7 C6 116.0(5) 2_765 . ? C7 C7 H6A 108.3 2_765 . ? C6 C7 H6A 108.3 . . ? C7 C7 H6B 108.3 2_765 . ? C6 C7 H6B 108.3 . . ? H6A C7 H6B 107.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C1 C2 O1 -67.3(3) . . . . ? Cl3 C1 C2 O1 171.0(3) . . . . ? Cl1 C1 C2 O1 52.9(3) . . . . ? Cl2 C1 C2 C3 51.1(3) . . . . ? Cl3 C1 C2 C3 -70.7(3) . . . . ? Cl1 C1 C2 C3 171.2(2) . . . . ? C4 O3 C3 O2 -1.0(5) . . . . ? C4 O3 C3 C2 178.2(3) . . . . ? O1 C2 C3 O2 13.1(4) . . . . ? C1 C2 C3 O2 -107.0(4) . . . . ? O1 C2 C3 O3 -166.1(3) . . . . ? C1 C2 C3 O3 73.9(4) . . . . ? C3 O3 C4 C5 77.7(4) . . . . ? O3 C4 C5 C6 60.4(4) . . . . ? C4 C5 C6 C7 -178.6(4) . . . . ? C5 C6 C7 C7 178.6(2) . . . 2_765 ? #END #------------------------------------------------------------------------------ data_(S,S)-21 _database_code_depnum_ccdc_archive 'CCDC 292300' _audit_creation_method SHELXL-97 _audit_update_record ; 2005-12-8 CheckCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common (+)-(S)-1-Phenylethylammonium-(S)-3,3,3-trichlorolactate _chemical_melting_point 399 _chemical_formula_sum 'C11 H14 Cl3 N O3 ' _chemical_formula_moiety 'C8 H12 N1, C3 H2 Cl3 O3 ' _chemical_formula_weight 314.58 _chemical_absolute_configuration rmad _chemical_optical_rotation '[\a]^20^~D~= +18.62 (c = 1.3, MeOH)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2129(1) _cell_length_b 6.6622(2) _cell_length_c 12.5141(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.890(2) _cell_angle_gamma 90.00 _cell_volume 745.63(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 2455 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.4 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_special_details ;Single crystal was grown in ethanol solution. A block crystal was mounted on a glass capillary. The data were collected at room temperature. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details ;NUMABS Higashi T. (1999) Program for absorption correction, Rigaku Corporation, Tokyo, Japan. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 4397 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.2074 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1778 _reflns_number_gt 1510 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.4 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atoms of NH3(+) and OH have been located from Fourier difference map and fixed to their positions. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.4132P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(16) _refine_ls_number_reflns 1778 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.394 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5203(5) 0.5189(8) 0.7932(4) 0.0498(11) Uani 1 1 d . . . C2 C 0.6388(5) 0.6431(8) 0.7569(4) 0.0472(10) Uani 1 1 d . . . H2 H 0.6857 0.5583 0.7106 0.057 Uiso 1 1 calc R . . C3 C 0.7631(5) 0.7224(8) 0.8538(4) 0.0468(11) Uani 1 1 d . . . C4 C 1.1398(9) 0.0492(13) 0.8004(7) 0.090(2) Uani 1 1 d . . . H4A H 1.2031 0.0169 0.8712 0.080 Uiso 1 1 calc R . . H4B H 1.1995 0.0614 0.7476 0.080 Uiso 1 1 calc R . . H4C H 1.0673 -0.0555 0.7780 0.080 Uiso 1 1 calc R . . C5 C 1.0606(6) 0.2452(9) 0.8077(5) 0.0558(13) Uani 1 1 d . . . H5 H 1.1367 0.3490 0.8324 0.067 Uiso 1 1 calc R . . C6 C 0.9579(6) 0.3146(10) 0.7000(4) 0.0547(12) Uani 1 1 d . . . C7 C 0.8369(8) 0.2011(13) 0.6467(5) 0.0730(17) Uani 1 1 d . . . H6 H 0.8186 0.0772 0.6751 0.080 Uiso 1 1 calc R . . C8 C 0.7434(9) 0.2715(19) 0.5516(6) 0.096(3) Uani 1 1 d . . . H7 H 0.6616 0.1939 0.5172 0.080 Uiso 1 1 calc R . . C9 C 0.7653(10) 0.446(2) 0.5070(5) 0.106(4) Uani 1 1 d . . . H8 H 0.6993 0.4906 0.4430 0.080 Uiso 1 1 calc R . . C10 C 0.8852(11) 0.5580(15) 0.5561(7) 0.100(3) Uani 1 1 d . . . H9 H 0.9038 0.6778 0.5236 0.080 Uiso 1 1 calc R . . C11 C 0.9818(7) 0.4969(11) 0.6550(5) 0.0661(15) Uani 1 1 d . . . H10 H 1.0611 0.5783 0.6899 0.080 Uiso 1 1 calc R . . Cl1 Cl 0.59341(17) 0.29139(19) 0.85391(14) 0.0707(5) Uani 1 1 d . . . Cl2 Cl 0.4426(3) 0.6501(4) 0.8877(2) 0.1171(9) Uani 1 1 d . . . Cl3 Cl 0.3778(2) 0.4533(4) 0.67781(18) 0.1049(9) Uani 1 1 d . . . N1 N 0.9731(5) 0.2248(7) 0.8919(4) 0.0451(9) Uani 1 1 d . . . O1 O 0.5698(5) 0.8051(8) 0.6932(4) 0.0835(15) Uani 1 1 d . . . O2 O 0.7670(5) 0.9035(6) 0.8689(5) 0.0798(15) Uani 1 1 d . . . O3 O 0.8508(4) 0.5998(6) 0.9092(3) 0.0577(10) Uani 1 1 d . . . H3A H 0.896(6) 0.150(9) 0.876(4) 0.040(13) Uiso 1 1 d . . . H3B H 0.927(7) 0.340(11) 0.893(5) 0.055(17) Uiso 1 1 d . . . H3C H 1.019(5) 0.183(7) 0.957(4) 0.029(11) Uiso 1 1 d . . . H1 H 0.6227 0.9074 0.7416 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(2) 0.052(3) 0.058(3) 0.006(2) 0.010(2) -0.001(2) C2 0.045(2) 0.047(2) 0.047(2) 0.009(2) 0.0048(18) 0.003(2) C3 0.043(2) 0.039(2) 0.056(3) 0.004(2) 0.007(2) 0.001(2) C4 0.089(5) 0.093(5) 0.099(5) 0.005(4) 0.041(4) 0.044(5) C5 0.049(3) 0.052(3) 0.063(3) 0.000(2) 0.007(2) 0.001(2) C6 0.054(3) 0.061(3) 0.050(3) -0.003(3) 0.015(2) 0.002(3) C7 0.080(4) 0.083(4) 0.055(3) -0.016(3) 0.014(3) -0.016(4) C8 0.084(5) 0.149(9) 0.047(3) -0.029(5) 0.003(3) -0.010(5) C9 0.092(5) 0.183(12) 0.041(3) 0.008(6) 0.010(3) 0.007(7) C10 0.127(7) 0.103(7) 0.080(5) 0.039(5) 0.043(5) 0.030(6) C11 0.064(3) 0.067(4) 0.070(4) 0.011(3) 0.021(3) 0.005(3) Cl1 0.0641(8) 0.0489(7) 0.0962(11) 0.0251(7) 0.0138(7) -0.0032(6) Cl2 0.1104(15) 0.1023(16) 0.167(2) -0.0297(16) 0.0880(15) 0.0094(13) Cl3 0.0679(9) 0.1210(18) 0.1016(13) 0.0299(13) -0.0270(9) -0.0418(12) N1 0.043(2) 0.0373(19) 0.047(2) -0.0041(18) -0.0048(17) 0.0040(19) O1 0.072(3) 0.071(3) 0.089(3) 0.043(3) -0.018(2) -0.010(2) O2 0.069(3) 0.0283(19) 0.127(4) -0.001(2) -0.007(3) -0.0013(17) O3 0.061(2) 0.0394(18) 0.059(2) -0.0081(16) -0.0133(17) 0.0088(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.523(7) . ? C1 Cl1 1.756(5) . ? C1 Cl2 1.756(6) . ? C1 Cl3 1.757(5) . ? C2 O1 1.401(6) . ? C2 C3 1.547(7) . ? C2 H2 0.9800 . ? C3 O2 1.220(7) . ? C3 O3 1.238(6) . ? C4 C5 1.509(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 N1 1.479(7) . ? C5 C6 1.521(8) . ? C5 H5 0.9800 . ? C6 C11 1.379(9) . ? C6 C7 1.380(9) . ? C7 C8 1.373(11) . ? C7 H6 0.9300 . ? C8 C9 1.326(16) . ? C8 H7 0.9300 . ? C9 C10 1.353(14) . ? C9 H8 0.9300 . ? C10 C11 1.401(10) . ? C10 H9 0.9300 . ? C11 H10 0.9300 . ? N1 H3A 0.86(6) . ? N1 H3B 0.88(7) . ? N1 H3C 0.86(5) . ? O1 H1 0.960 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 Cl1 111.7(3) . . ? C2 C1 Cl2 111.6(4) . . ? Cl1 C1 Cl2 108.3(3) . . ? C2 C1 Cl3 109.8(4) . . ? Cl1 C1 Cl3 105.9(3) . . ? Cl2 C1 Cl3 109.4(3) . . ? O1 C2 C1 109.2(4) . . ? O1 C2 C3 109.4(4) . . ? C1 C2 C3 113.6(4) . . ? O1 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? C3 C2 H2 108.2 . . ? O2 C3 O3 125.0(5) . . ? O2 C3 C2 116.6(5) . . ? O3 C3 C2 118.3(4) . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C4 108.5(5) . . ? N1 C5 C6 109.2(4) . . ? C4 C5 C6 114.6(5) . . ? N1 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? C11 C6 C7 118.4(6) . . ? C11 C6 C5 120.2(6) . . ? C7 C6 C5 121.4(6) . . ? C8 C7 C6 119.9(8) . . ? C8 C7 H6 120.1 . . ? C6 C7 H6 120.1 . . ? C9 C8 C7 122.5(8) . . ? C9 C8 H7 118.8 . . ? C7 C8 H7 118.8 . . ? C8 C9 C10 118.9(8) . . ? C8 C9 H8 120.6 . . ? C10 C9 H8 120.6 . . ? C9 C10 C11 121.2(9) . . ? C9 C10 H9 119.4 . . ? C11 C10 H9 119.4 . . ? C6 C11 C10 119.1(7) . . ? C6 C11 H10 120.4 . . ? C10 C11 H10 120.4 . . ? C5 N1 H3A 117(3) . . ? C5 N1 H3B 106(4) . . ? H3A N1 H3B 98(5) . . ? C5 N1 H3C 118(3) . . ? H3A N1 H3C 102(5) . . ? H3B N1 H3C 113(5) . . ? C2 O1 H1 95.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl1 C1 C2 O1 170.2(4) . . . . ? Cl2 C1 C2 O1 -68.4(5) . . . . ? Cl3 C1 C2 O1 53.1(5) . . . . ? Cl1 C1 C2 C3 -67.4(5) . . . . ? Cl2 C1 C2 C3 54.0(5) . . . . ? Cl3 C1 C2 C3 175.4(4) . . . . ? O1 C2 C3 O2 10.2(7) . . . . ? C1 C2 C3 O2 -112.0(6) . . . . ? O1 C2 C3 O3 -169.4(5) . . . . ? C1 C2 C3 O3 68.4(6) . . . . ? N1 C5 C6 C11 117.3(5) . . . . ? C4 C5 C6 C11 -120.7(7) . . . . ? N1 C5 C6 C7 -60.8(7) . . . . ? C4 C5 C6 C7 61.2(8) . . . . ? C11 C6 C7 C8 -0.4(10) . . . . ? C5 C6 C7 C8 177.7(6) . . . . ? C6 C7 C8 C9 0.8(12) . . . . ? C7 C8 C9 C10 0.8(14) . . . . ? C8 C9 C10 C11 -2.8(14) . . . . ? C7 C6 C11 C10 -1.5(9) . . . . ? C5 C6 C11 C10 -179.6(6) . . . . ? C9 C10 C11 C6 3.1(12) . . . . ? #END